N-(4-azidobutyl)phthalimide | 66917-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(4-azidobutyl)phthalimide
• 英文别名: 2-(4-azidobutyl)isoindoline-1,3-dione；(phthalimido)butyl azide；2-(4-azidobutyl)isoindole-1,3-dione
• CAS: 66917-06-4
• 化学式: C₁₂H₁₂N₄O₂
• 分子量: 244.253
• InChiKey: ORKCIOAZJQNDJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-azidobutyl)phthalimide 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以70%的产率得到N-(4-氨基-1-丁基)邻苯二甲酰亚胺盐酸盐
  参考文献：
  名称：

  .alpha.-Methyl polyamines: metabolically stable spermidine and spermine mimics capable of supporting growth in cells depleted of polyamines

  摘要：

  In order to assess the tolerance of the target enzyme spermine synthase for alpha-substituents on the aminopropyl moiety of the substrate spermidine, 1-methylspermidine (MeSpd, 2) was synthesized. It was determined that MeSpd is a poor substrate for spermine synthase and is not a substrate for spermidine N1-acetyltransferase, suggesting that alpha-methylated polyamines might be metabolically stable and therefore useful tools for studying polyamine effects in intact cells. On the basis of initial cellular results with 2, 1-methylspermine (MeSpm, 3) and 1,12-dimethylspermine (Me2Spm, 4) were also synthesized. When added to cells (L1210, SV-3T3, or HT29) depleted of both putrescine and spermidine by prior treatment with alpha-(difluoromethyl)ornithine (DFMO), these alpha-methylated polyamines were able to restore cell growth to that observed in the absence of DFMO. In accord with the enzyme data noted above, metabolic studies indicated a slow conversion of 2 to 3, but no metabolism of 4 in these cells. It was concluded from these results that the alpha-methylated polyamines are able to substitute for the natural polyamines spermidine and spermine in critical biochemical processes which involve polyamines for continued cell growth. In accord with the hypothesis, preliminary data indicate that MeSpd and Me2Spm are as effective as spermidine and spermine, respectively, in promoting the conversion of B-DNA to Z-DNA.

  DOI：

  10.1021/jm00082a013
• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 在 sodium azide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 N-(4-azidobutyl)phthalimide
  参考文献：
  名称：

  通过点击反应合成新颖的1,4-二取代-1,2,3-三唑福司可林半合成类似物

  摘要：

  在1位上进行区域选择性炔丙基化反应，然后在Cu（I）催化下，Cu（I）催化环加成不同的烷基叠氮化合物，制备了新的Forskolin（5a - g，6a - g）1,4-二取代-1,2,3-三唑类似物。单击反应条件。碱催化的炔丙基化中一个有趣的酰基转移提供了一系列新的毛喉素1,4-二取代-1,2,3-三唑类似物（6a – g）。这些类似物作为抗高血压药，抗青光眼，抗哮喘和抗肥胖药具有潜在的选择性治疗应用。

  DOI：

  10.1016/j.tetlet.2011.08.154

文献信息

• 二苯并磷杂茂化合物及其合成方法和应用
  申请人：华东师范大学

  公开号：CN107188906B

  公开（公告）日：2019-06-14

  本发明公开了新的二苯并磷杂茂式(I)及其制备方法。二苯并磷杂茂式(I)根据苯环上R2和R2′取代基的不同分为式(II)、式(III)和式(IV)三大类。本发明式(II)二苯并磷杂茂的合成方法，从简单且易制备的原料A出发通过双锂化‑环化串联反应高效构建，反应条件温和，有较好的官能团兼容性。式(II)可通过Pd催化的Sonogashira偶联‑脱硅串联反应高效制备式(III)二苯并磷杂茂。式(IV)可通过式(II)或式(III)经常规转化而来。本发明还提出了式(III)化合物通过进一步发生不对称去对化CuAAC反应得到含三氮唑的手性磷杂茂的应用。本发明二苯并磷杂茂化合物可作为潜在光电材料应用于光学器件中。
• Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes
  作者：Xuelun Duan、Nan Zheng、Ming Li、Xinhao Sun、Zhuye Lin、Pan Qiu、Wangze Song

  DOI：10.1016/j.cclet.2021.05.037

  日期：2021.12

  5-regioselectivities and excellent chemoselectivities. Ether group could coordinate with iridium catalyst by lone-pair electron at a distance (up to four σ bonds) away from alkyne to control the regioselectivity by weak coordination effect. The cycloaddition reaction chemoselectively occurred at the propargyl ether moiety of diyne to give unique fully substituted 4-alkynyl-triazole.

  远程醚基团可以用作制备具有唯一的1，5-区域选择性和优异的化学选择性的完全取代的5-醚-1,2,3-三唑的指导基团。醚基可以通过孤对电子在距炔烃一定距离（最多4个σ键）的情况下与铱催化剂配位，从而通过弱配位效应控制区域选择性。在二炔的炔丙基醚部分发生化学选择性的环加成反应，得到独特的完全取代的4-炔基-三唑。
• Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins
  作者：Hongze Li、Shou-Jie Shen、Cheng-Liang Zhu、Hao Xu

  DOI：10.1021/jacs.9b04381

  日期：2019.6.12

  hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation

  我们在此报告了一种用于未活化烯烃的直接分子间抗马尔科夫尼科夫加氢叠氮化方法，该方法在环境温度下由催化量的长期稳定的苯并恶醇促进。这种方法有助于在复杂分子和未官能化的商品化学品中跨各种未活化的烯烃直接添加重氮酸，这是以前困难的。它方便地填补了现有烯烃氢叠氮化程序的合成化学空白，从而为有机合成和化学生物学研究中的叠氮基标记提供了有价值的工具。
• Synthesis of New Hybrid Heterocyclic Compounds Having 1,2,3-Triazole and Isoxazole via Click Chemistry
  作者：Y. Jayaprakash Rao、A. Srinivas

  DOI：10.1002/jhet.1798

  日期：2014.11

  A simple and highly efficient method for the regioselective synthesis of isoxazolyl‐1,4‐disubstituted‐1,2,3‐triazoles 6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j, 6k, 6l in good to excellent yields from terminal alkynes having isoxazole scaffold 4a, 4b, 4c and various azides through Cu(I)‐catalyzed 1,3‐dipolar cycloaddition is described. The reaction proceeds smoothly in 1:1 mixture of t‐BuOH and water

  一种简单高效的区域选择性合成异恶唑基-1,4-二取代-1,2,3-三唑6a，6b，6c，6d，6e，6f，6g，6h，6i，6j，6k，6l的方法描述了具有异恶唑骨架4a，4b，4c和各种叠氮化物的末端炔烃通过Cu（I）催化的1,3-偶极环加成反应的良好至优异的收率。反应在t的1：1混合物中平稳进行-室温下加BuOH和水。根据光谱数据ir，1 H nmr，质量和元素分析，确定所有新合成的杂合杂环的结构。
• 3,6-Bicyclolides
  申请人：Or Sun Yat

  公开号：US20060122128A1

  公开（公告）日：2006-06-08

  The present invention discloses compounds of formula (I) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

  本发明公开了具有以下结构的化合物（I）或其药学上可接受的盐、酯或前药： 具有抗菌性能。本发明还涉及包含上述化合物的药物组合物，用于给需要抗生素治疗的受试者使用。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的细菌感染的方法。该发明还包括制备本发明化合物的方法。